# US 7,608,671 B2 · Norbornene ring-opened polymer hydrogenated product and process for producing same

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- Number: US 7,608,671 B2
- Document ID: US7608671B2
- Status: Granted
- Kind: B2
- Application number: 10/567,964
- Filed: 2004-08-12
- Published: 2007-08-09
- Granted: 2009-10-27
- Earliest claimed: 2003-08-13
- Assignees: Zeon Corporation
- Inventors: Shigetaka Hayano; Yasuo Tsunogae
- Web page: https://patentgrep.com/patent/US7608671B2

## CPC

- C08G 61/06: prepared by ring-opening of carbocyclic compounds
- C08G 61/08: of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
- C08G 2261/3324: derived from norbornene
- C08G 2261/3325: derived from other polycyclic systems
- C08G 2261/418: Ring opening metathesis polymerisation [ROMP]
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A norbornene ring-opened polymer hydrogenated product having a syndiotactic structure and a process for producing the same are disclosed. The ring-opened polymer hydrogenated product contains a repeating unit originating from a polycyclic norbornene monomer with three or more rings in the polymer repeating units, having a weight average molecular weight of 500 to 1,000,000, and having a racemo diad proportion of 51% or more. The process comprises a step of polymerizing a polycyclic norbornene monomer having three or more rings by solution polymerization using a group 6 transition metal compound with a hydroxyl group-containing aryloxy group or the like bonded thereto as a polymerization catalyst to obtain a ring-opened polymer and a step of hydrogenating double bonds in the main chain of the ring-opened polymer.

## Claims

### Claim 1

A ring-opened polymer hydrogenated product containing a repeating unit originating from a polycyclic norbornene monomer with three or more rings in the polymer repeating units, having a weight average molecular weight of 25,000 to 1,000,000, and having a racemo diad proportion of 70% or more.

### Claim 2 (depends on 1)

The ring-opened polymer hydrogenated product according to claim 1, wherein the content of the repeating unit originating from a polycyclic norbornene monomer with three or more rings is 50 mol % or more.

### Claim 3 (depends on 1)

The ring-opened polymer hydrogenated product according to claim 1, wherein the repeating unit originating from a polycyclic norbornene monomer with three or more rings is a repeating unit originating from dicyclopentadiene.

### Claim 4 (depends on 1)

The ring-opened polymer hydrogenated product according to claim 1, which is a crystalline polymer.

### Claim 5 (depends on 4)

The ring-opened polymer hydrogenated product according to claim 4, which is a polymer having a melting point of 150° C. or more.

### Claim 6 (depends on 1)

A process for producing the ring-opened polymer hydrogenated product according to claim 1, comprising a step of polymerizing a polycyclic norbornene monomer having three or more rings by solution polymerization using a compound shown by the following formula (a) as a polymerization catalyst to obtain a ring-opened polymer and a step of hydrogenating double bonds in the main chain of the ring-opened polymer,
M(NRa)X3Y.Lb (a)
wherein M is tungsten, Ra is a substituted or unsubstituted phenyl group with a substituent at any of 3, 4, or 5 position or a group represented by CH2Rd, wherein Rd indicates a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, X represents a halogen atom; alkyl group, aryl group, or alkylsilyl group, Y is a hydroxyl group-containing aryloxy group or a hydroxyl group-containing alkoxyl group, L is an electron donating neutral ligand, and b is an integer of 0 to 2.

### Claim 7 (depends on 1)

A process for producing the ring-opened polymer hydrogenated product according to claim 1, comprising a step of polymerizing a polycyclic norbornene monomer having three or more rings by solution polymerization using a compound shown by the following formula (b) as a polymerization catalyst to obtain a ring-opened polymer and a step of hydrogenating double bonds in the main chain of the ring-opened polymer,
M(NRb)X4-a(ORc)a.Lb (b)
wherein M is tungsten, Rb is a substituted or unsubstituted phenyl group with a substituent at any of 3, 4, or 5 position or a group represented by CH2Rd, wherein Rd indicates a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, X represents a halogen atom, alkyl group, aryl group, or alkylsilyl group, Rc is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, L is an electron donating neutral ligand, a is 0 or 1, and b is an integer of 0 to 2.